Cesium carbonate → HCID 86726513, compound

HRID 1487686Notes

Reaction equation

HRID 1487686 reaction equation
Cl[C:2]1[N:3]=[C:4]([O:29][CH:30]2[CH2:33][C:32]([F:35])([F:34])[CH2:31]2)[C:5]2[C:10]([C:11]3[CH:20]=[CH:19][C:14]([C:15]([NH:17][CH3:18])=[O:16])=[CH:13][CH:12]=3)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=2[N:7]=1.[NH2:36][C:37]1[CH:49]=[CH:48][C:40]([C:41]([NH:43][CH:44]2[CH2:47][O:46][CH2:45]2)=[O:42])=[CH:39][C:38]=1[O:50][CH3:51].C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>O1CCOCC1.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CO>[F:34][C:32]1([F:35])[CH2:33][CH:30]([O:29][C:4]2[C:5]3[C:10]([C:11]4[CH:20]=[CH:19][C:14]([C:15](=[O:16])[NH:17][CH3:18])=[CH:13][CH:12]=4)=[CH:9][N:8]([CH2:21][O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])[C:6]=3[N:7]=[C:2]([NH:36][C:37]3[CH:49]=[CH:48][C:40]([C:41]([NH:43][CH:44]4[CH2:45][O:46][CH2:47]4)=[O:42])=[CH:39][C:38]=3[O:50][CH3:51])[N:3]=2)[CH2:31]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 867264484-Amino-3-methoxy-N-(oxetan-3-yl)benzamideHCID 86726512HCID 86726512, compound

Product 1

HCID 86726513HCID 86726513, compoundYield 78.3%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4-(2-chloro-4-(3,3-difluorocyclobutoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-N-methylbenzamide (1 equiv), 4-amino-3-methoxy-N-(oxetan-3-yl)benzamide (1 equiv), and cesium carbonate (3 equiv) in 1,4-dioxane (0.1 M) was degassed with N2 for 10 min. Then (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.2 equiv), tris(dibenzylideneacetone)dipalladium(0) (0.1 equiv), were added to this mixture. The mixture was stirred at 140° C. for 1.5 h. After cooling to room temperature, the reaction mixture was purified using silica gel chromatography (0-100% ethyl acetate in hexane then 0-20% MeOH in DCM) to afford the title compound (78.3% yield). MS (ESI) m/z 709.4 [M+1]+.

Workup

  1. customwas degassed with N2 for 10 min
  2. temperatureAfter cooling to room temperature
  3. customthe reaction mixture was purified

Sources & evidence

ORD record
ord-7107bd73aaf54a02b9cf36aacff5b577
Source dataset
uspto-grants-2016_08
Patent number
US09428509B2

Reaction notes

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